Jonathan Joseph of Little Red Fashion: “Know the problem you’re solving”

Too often, I think tech founders want to run before we walk. We’re so excited about what we’re doing that we don’t always allow ourselves the space to do deep research and learn from it. With Little Red Fashion I was so caught up in packing our first drafts of The Little Red Dress with […]

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Too often, I think tech founders want to run before we walk. We’re so excited about what we’re doing that we don’t always allow ourselves the space to do deep research and learn from it. With Little Red Fashion I was so caught up in packing our first drafts of The Little Red Dress with vocabulary words and a fat glossary of terms that I completely forgot about this little thing called readability. If kids can’t get through the book because it keeps getting broken up, how am I actually teaching them? In that instance I was solving the problem of the side dishes instead of focusing on the main course. A few surveys from educators later and we nixed the glossary but worked elements of it into our reading comprehension and literacy e-book concept. Same stuff, new format, better reception! In our excitement to teach kids about fashion, we didn’t solve a baseline issue of readability. Which leads me into my next thing:

In recent years, Big Tech has gotten a bad rep. But of course many tech companies are doing important work making monumental positive changes to society, health, and the environment. To highlight these, we started a new interview series about “Technology Making An Important Positive Social Impact”. We are interviewing leaders of tech companies who are creating or have created a tech product that is helping to make a positive change in people’s lives or the environment. As a part of this series, I had the pleasure of interviewing Jonathan Joseph.

Jonathan Joseph is the creator and CEO of Little Red Fashion, the first EdTech and publishing company focused on empowering kids 8–14 who love fashion. A longtime strategic consultant & fundraiser in the philanthropic and private sectors, Jonathan formally launched LRF in July of 2020 after completing the first of their 12 titles “The Little Red Dress: A Kids Book About Fashion” Jonathan splits his time between Connecticut and Los Angeles and is also an abstract fine artist.


Thank you so much for joining us in this interview series. Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your childhood backstory and how you grew up?

I was born in Medellin Colombia in 1986 and apparently left at an orphanage until the age of 9 months where I was adopted by my parents. I grew up in the NYC suburbs of Connecticut and wasn’t told the truth about my heritage until about the age of 11. My dad is an academic from Tehran, Iran and my mom is your classic NYC Italian/Irish woman with a quick wit and tenacious drive. I take after her. I grew up rather happy-go-lucky and have apparently not shut up since my first word (which was “hi.)” I was made to be social I guess. I have ataxic cerebral palsy, the rarest form, which affects my depth perception, balance and motor skills. My disability is actually where my love of fashion started. My mom did her best to downplay my AFO leg braces by taking me through the garment district to find long socks to cover them which matched or complimented my outfits. Our shopping exploits launched my love of color and style. For me it wasn’t about hiding my braces, it was about owning them making them a statement. As I aged out of physical and occupational therapy as well as my braces a new-to-me “othering” was brewing.

I grew up LGBTQIA+ in the age of Matthew Shepard. It instilled in me a fire for social justice that carries through to this day and informed my studies in philanthropy and CSR at Columbia and was how I got started as an activist. First on anti-semitism at my temple, then about homophobia and its impact for organizations like the ADL. Classmates of mine can recount the endless ways I was harassed or assaulted by bullies over the years, but I never lost my voice. I thank my mother for that. You could say it’s also a huge part of why Little Red Fashion has a commitment to DE & I at our core as well. Her lessons on personal empowerment is part of the inspiration behind our tagline. Kids are taught to hate and grown ups need more tools to fight that. Knowledge after all, is power.

For anyone reading who grew up with a terminally ill parent, or …or anyone who’s dealing with a future loss of this nature I want them to know that it gets better. Losing my mother as a teenager was a watershed moment in my youth and for as many challenges it brought it also forged me into the leader I am today. It gets better, but don’t make the mistake I did at the time: reach out for help navigating your grief even if you don’t think you need it. I wish someone had told me that then. A huge part of why I’m doing what I do at LRF is to give kids and grown ups new ways of brokering tough conversations that can lead to healing or prevent trauma in the first place in a way only fashion can. I’m not alone either, just look at Christian Allaire’s recent book The Power of Style which does this amazingly. I highly recommend it to any grown up that has kids in their life that they love

Can you share the most interesting story that happened to you since you began your career?

Overall, I think what’s been most interesting as a professional fundraiser and strategic consultant has been the wide variety of industries I’ve been exposed to alone. Fashion yes of course, but also commodities, international logistics, entertainment, legal cannabis, and even music. One story that jumps out immediately has to do with one of our cannabis clients a few years back. We were approached just shy of 2 weeks before a permit application due date by a group who did not have their ducks in a a row. We had almost no time to gut their model, re-fashion it, bring in advisors and a new operations team AND help secure 5M dollars in capital. Somehow, our team pulled it off. I don’t recall there being very much sleep but what I do recall vividly is the day my business partner Ryan forced me to step away from writing and said, “how about you go work on that book about the dress? Take a break.” Without that break, I wouldn’t have finished our first book The Little Red Dress. It just goes to show you that you never know where today’s project will take you in the future.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I couldn’t agree more. Cultivating success is all about finding mentors who engage and inspire you. For me one that absolutely jumps out comes early in my life. I had a social studies teacher in high school, we’ll call him Mr. K. I’ve always been outspoken and articulate by nature, he saw that and without my knowledge signed me up for a leadership program that sent me to NYC, DC, China, and Europe over the next 4 years and allowed me to hone my keynote skills, diplomatic skills, and writing prowess. If not for those early opportunities to step behind a podium, I don’t know how my natural talents would have developed. I bring this up because I’m always obsessed with reminding grown ups just how vital their role is in providing conduits for success to kids even through what may seem in the moment like a small gesture.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

This one is easy, because I literally carry it in my wallet on the back of my mother’s Mass card since 2006 when she passed: “I shall pass through this world but once, any good therefore that I can or any kindness I can show to any creature, let me do it now, for I shall not pass this way again.” As a Buddhist since 2007 or so, that might seem at odds, but I take it to mean that you have but one shot to leave a positive impact. Every thing I do from advising boards or sitting on them to helping empower small businesses or create new tools through Little red Fashion I do through the perspective of this quote. Am I leaving the industries I affect better? Am I helping level the playing field or create access? This quote is my litmus test for life and for business.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

Being okay with“no”: As a professional fundraiser, one of the first things I learned from a mentor in grad school was that *everything* is a numbers game; as such if you can’t handle a “no” you can’t handle fundraising, entrepreneurship, most forms of consulting, and a slew of other things. Moreover, you have to be able to handle a long string of them in a row without letting it wear you down so you can get to the “yes” you need. I have failed a million times, I continue to fail (as we all do) even amidst other successes. In today’s media soaked landscape its easy to fall for the curatorial fallacy of perfection that our algorithms force feed us. Embrace your failures and learn from them, own them. It makes it all the more powerful when you push through to success. Just look at our stunning illustrations! It took over 40 “no”s to get to the “yes” that was Silvan who breathed life into my story and set our aesthetic baseline! All those no’s became worth it!

Gratitude: When you’re essentially born into an orphanage with something like CP, you get really used to chalking up the wins as they happen. Maybe that’s why I’ve always been so grateful for every opportunity or connection I’ve been given. My parents instilled a sense of gratitude in me that has been instrumental to my professional trajectory. It’s also something that’s deceptively simple to cultivate. If you ever get a professional email from me you’ll notice that I sign all of them, “appreciatively” because it’s a small subtle way to make sure anyone doing anything with or for me knows their presence and contributions matter to me very deeply. Gratitude also makes my first point about being okay with “no” a lot more easy!

Radical Honesty/Transparency: You cannot please everyone. You cannot be all things to all people. Part of living that truth a commitment to radical honesty about yourself, your business, and everything you do that affects your team and the community. It also means being honest with yourself. Success is about learning to navigate the world while maintaining a commitment to this key piece of the puzzle. If people know you’re radically transparent, if you are an open book more often than a siloed secret keeper it becomes so much easier to team-build or create collective impact. I’ve always been a huge fan of Ray Dalio’s Principles and this one I think is one of the most important things I learned from him. We even have clients teams read a copy or excerpts I keep in the office because I think they’re so effective. Mistakes happen, be honest about them and demonstrate the systems you create to prevent their repetition. That’s what most people are looking for, and it extends to admitting when you don’t know something and empowering those who do to help with your decision making process. Building teams around your weaknesses to compliment your strengths also takes radical honesty about where and why you fall short.

Ok super. Let’s now shift to the main part of our discussion about the tech tools that you are helping to create that can make a positive social impact on our society. To begin, what problems are you aiming to solve?

The fashion industry is guilty of many sins from perpetuating problematic tropes re: cultural appropriation to promoting unrealistic body image, contributing to exploitation of the global south to enable the fast fashion system or the rampant tokenization/racism, and ableism. It’s also guilty of having such a high barrier to entry way too much talent is simply left out of the running because they lack the money or connections to even get a foot in the door. We are here to end the worst of fashion culture while celebrating the best and empowering its more equitable future. It is an art form after all.

Changing the uncomfortable truths about fashion starts with making the field overall more accessible. Changing our industry values begins with better fashion education. It begins with realizing that kids who love fashion have never had comprehensive educational tools for fashion history, production, design and even simple things like mending. I love YouTube as much as the next person but, we can do better. Little Red Fashion is taking this notoriously insular industry as the focus of EdTech solutions that involve turning augmented reality from a gimmick to a genuine tool for immersive learning; we’re using fashion as the fodder for a slew of STEAM & literacy educational workbooks and videos, we’re creating a fashion Mentorship database and AI to power our fashion focused games.

Little Red Fashion’s tech is giving the grown ups who have fashion loving kids in their lives resources a generation overdue and meeting digitally native kids where they’re at: tablets, the metaverse, and beyond.

How do you think your technology can address this?

Fashion is complex, complicated, and brings together a lot of topics under one umbrella. AR enhanced books can make this more manageable and unlike traditional publishing can be updated and improved over time. This turns a formerly static resource into a long-term one packed with evolving value. Our fashion mentorship database in development can help kids & families from anywhere get key insights from professionals across the field in over a dozen disciplines that may inspire them. That used to mean you “need to know somebody” with that knowledge. Our deeper tech includes some things I can’t go into just yet (or my board will kill me) but sufficed to say we’re actively working to give kids a totally new type of control over the creative side of fashion design & practical side of fashion history through smart devices and IoT offerings for textile education.

Can you tell us the backstory about what inspired you to originally feel passionate about this cause?

There are two answers to this. One direct, and the other indirect.

Directly speaking, I was doing some consulting in luxury womenswear in New York City a few years ago, I had a client that was filled to the brim with many of the most toxic views of the industry. To put it succinctly this person’s creativity stopped at a size 4. I was party to conversations they’d have about how perfectly healthy girls were too fat, watched them laugh behind the backs of their own made to measure clients about their size or appearance and more. It reached a boiling point and I terminated the contract. A few months prior to that I had floated the idea of a kids book about fashion in the workroom and this client shared they too had wanted to do that. So that kicked off me writing the first draft of The Little Red Dress. After that, I started doing market research to guide my next steps and was INSTANTLY annoyed at how nobody had ever come up with a fashion education solution for kids. I got so annoyed that what started as a fun book is now Little Red Fashion. Eleanor Lambert, founder of the CFDA (Council of Fashion Designers of America) famously said, “You must always be alert and see the things right in front of you that are not being done and should be done.” So I am. Because 9 year old me made me do it. Your readers should definitely check out my piece about LRF published by the CFDA here, by the way.

Indirectly so, my mother. My mother’s indomitable fight to make her disabled son feel empowered through clothing to counter the bullying about his leg braces inspired me. Her own use of clothing and dress to lift herself up in her darkest moments (especially this one pair of vintage Dior sunglasses she used to wear to chemo infusions) inspired me to feel passionately about giving fashion the respect as a field of study and artistic discipline that it deserves.

How do you think this might change the world?

Our tech can change the world by truly democratizing a trillion dollar industry in a way only truly empowered young people can. It can change the world by creating a truly conscious generation of consumers who see through greenwashing and performative allyship damaging the planet and various social movements. It can change the world by showing kids who are also feeling unseen like I did that people like them are out here thriving and living their best lives. Right now I’m in the thick of writing our second title The Little Red Kit all about sportswear, technical fabric, and the history of soccer kits/insignia through the eyes of a kid with cerebral palsy like me and his best friend Liam. We’re courting all sorts of amazing partner authors for similarly diverse books that dovetail fashion with social impact to change the world one story at a tie. Our AR and other tech will allow these inspired kids to take that energy and focus it in completely new ways. Our later top secret tech in development can change the way cultural or educational institutions and archives teach fashion to the public at large. Little Red Fashion has the potential to use tech as a democratizing force for fashion like never before. The truth is if we can do it for fashion, we can also use our core tech and trade secrets to help other high barrier to entry industries lead their next generation of professionals too.

Keeping “Black Mirror” and the “Law of Unintended Consequences” in mind, can you see any potential drawbacks about this technology that people should think more deeply about?

No, honestly I don’t I see no potential drawback to making books more interactive through augmented reality and creating smart tools for textile education. I don’t see a Black Mirror of fashion moment where our mentorship AI becomes sentient and runs amok. But what I do see is the need to be equally as committed to making more tech available to more kids from disadvantaged backgrounds.

What I see is that as a tech company focused on education we must always be working to meet new foundations or charitable individuals willing to help us do that as partners in our Little Red Literacy program. What I see is that fashion ed tech is a win-win situation for kids, grown ups, and the industry at large, but that as such we need to make sure when we say “Fashion is for Everyone” we truly mean “Everyone” and do anything we can to expand that definition over time. Do I think we can get a smartphone or tablet to every kid out there? Maybe not. But we can advocate for better funding in classrooms, we can advocate for more library programs, we can work with charitable partners to provide free copies of our books available or create fashion learning experiences open to the public. Collective impact and collaboration are the ways we prevent our tech from becoming another tool of exclusion in the world of fashion. I talk even more about the future state of Little Red Fashion in my interview with “the gold standard” in fashion podcasting Dressed: The History of Fashion which you can check out here.

Here is the main question for our discussion. Based on your experience and success, can you please share “Five things you need to know to successfully create technology that can make a positive social impact”? (Please share a story or an example, for each.)

  • Social impact requires genuine social equity

It is 2021, there is too much capital floating around to merely tack on social impact as an afterthought as many companies do. For one thing it’s disingenuous, but moreover it’s a missed opportunity to solve serious problems particularly in the world of tech. We all know (unless we’re under a rock) that women, LGBTQIA+ folks, and people of color are vastly underrepresented in C suites and on cap tables. At Little Red Fashion that’s why our cap table is as diverse as the audiences we’re trying to reach. There is nothing I hate more than performative bumper sticker CSR and empty buzzwords. Put your money where your values are. Positive social impact isn’t just cute verbiage, it means taking issues to the mat. If you look around C suite/your board and everyone looks the same, you’re already doing social impact in this century very wrong.

  • Know the problem you’re solving

Too often, I think tech founders want to run before we walk. We’re so excited about what we’re doing that we don’t always allow ourselves the space to do deep research and learn from it. With Little Red Fashion I was so caught up in packing our first drafts of The Little Red Dress with vocabulary words and a fat glossary of terms that I completely forgot about this little thing called readability. If kids can’t get through the book because it keeps getting broken up, how am I actually teaching them? In that instance I was solving the problem of the side dishes instead of focusing on the main course. A few surveys from educators later and we nixed the glossary but worked elements of it into our reading comprehension and literacy e-book concept. Same stuff, new format, better reception! In our excitement to teach kids about fashion, we didn’t solve a baseline issue of readability. Which leads me into my next thing:

  • Create as many feedback loops as possible

Nothing is more valuable than feedback from the people who support you early, that includes advisors, reviewers or anyone. Our parent and educator feedback loops the past two years have gotten us to where we are. Little Red Fashion might be officially less than a year old, but I’ve been getting feedback on the core concepts for almost 4 years now! Without them we wouldn’t have come up with some of our textile education smart tools! Without feedback loops and questionnaires or direct emails about concepts we thought were great, we wouldn’t be dipping our toes into the NFT and animated content space. Never forget, asking is always free and doing so really puts the social in social impact.

  • Community-building is the only way forward

Speaking of social, tech for social good must be community focused. Technologists looking to solve social issues need to make sure that they’ve got enough community involvement to cover the spread of opinions so to speak. In a pluralistic society it behooves a social impact tech founder to have as many diverse voices as possible as part of broad conversations that drive more nuanced decision making. Having more diverse seats at the decision making table then allows those voices to be heard and championed appropriately. No social impact company in 2021 will get anywhere without building a community as consumers today are finally starting to see through performative lazy CSR and other symbolic ways many companies placate critics. Organic community building is the best way to grow in my opinion. For us at Little Red Fashion that means building our community of fashion loving professionals who feel as I do that our tools are the things they wish they’d had. We do this through our Little Red Village project. We’ve found this translates into a core network of supporters who spread our mission and grow our mission and grow our mentorship database

  • Iteration not perfection: flexibility is everything

Things don’t always look the way you thought they would. Tech is about iteration and improvement not nailing it perfectly right off the bat. The fact is you’re not always going to like what you put out there in every way but without objective feedback it’s all just echo chamber noise. When I first conceived of Little Red Fashion I was dead set on creating a kids sketchpad off the bat because it was “obvious” to me. But that was a miscalculation. A few months into our prototype it occurred to me that we’re reinventing the wheel and can hold off until a later fundraising round to acquire a sketchpad tech firm. This was corroborated by dozens of conversations with industry professionals who were so much more keen on our mentorship AI and game offering which is where we’ve pivoted our energy since. Especially when your endgame is social impact, you have to be feedback driven and not worry about the negative feedback you need to grow.

If you could tell other young people one thing about why they should consider making a positive impact on our environment or society, like you, what would you tell them?

Chalk this up to being a Buddhist but like so many things, it comes down to compassion. Having compassion for the planet and for those among us who are marginalized or disenfranchised puts us into a mindset of service and empathy. Make the choice to live in this headspace consciously and with healthy boundaries for self-care and there is no limit to what you can accomplish. No matter what your passions and talents are you can find a way to tailor them to the broader needs of the world and society while living your truth and being excited about it. As the Dalai Lama says, “If you want others to be happy, practice compassion. If you want to be happy, practice compassion.” Don’t be like me, or anyone else for that matter. Just be the best you that you can be and align your passions with the problems you want to solve.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. 🙂

Michelle Obama, hands down. She’s a quintessentially inspiring erudite scholar, fashion maven, FLOTUS, and activist for the causes she cares about. Full disclosure, she’s ALSO why the little red dress itself is named Michelle! She’s just *that* inspiring to myself and a whole generation of those committed to social justice with a bit of style. I’d ask her how she feels the American system of philanthropy can be improved, how we can create better digital infrastructure for low income kids & their families and how we can use technology to solve issues like food desserts and early childhood nutrition which negatively impact the academic performance of too many children. Lastly, I’d ask her how she feels the American fashion industry can better support creatives from historically marginalized groups and more proactively solve the systemic issues of fast fashion we’ve exported across the globe. You know, light banter.

How can our readers further follow your work online?

Little Red Fashion can be found on Instagram at @LittleRedFashionCo or www.LittleRedFashion.com where they can pre-order a digital copy of The Little Red Dress and join our mailing list to find out when our hardcover AR enhanced special editions are available for pre-order. Together, one story or download at a time we can empower the next generation of fashion lovers, leaders, and creatives together. And, if they really want to help us reach our goal of 850 print sales of our amazing artwork they can check that out on our website shop as well! Three of our iconic pages are available as glicée prints measuring 18” x 12” both framed and unframed. Print sales fund our expanded educational material development!

Thank you so much for joining us. This was very inspirational, and we wish you continued success in your important work.

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